2: pyridinium chlorochromate; NaOAc; molecular sieves / CH2Cl2 / 1 h / Ambient temperature 3: 1.) n-BuLi in n-hexane/diisopropylamine / 1.) THF, -74 deg C, 80 min,2.) -70 deg C, 30 min 4: 84 percent / (i-Pr)2NEt / CH2Cl2 / 89 h / Ambient temperature 5: 82 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 6: 84 percent / quinoline; H2 / 5percent Pd/BaSO4 / methanol / Ambient temperature 7: LiOH*H2O / H2O; tetrahydrofuran / 5 h / Ambient temperature 8: 1.) 2,4,6-trichlorobenzoyl chloride, NEt3,2.) 4-(dimethylamino)pyridine / 1.) THF, room temp., 8.5 h, 2.) toluene, reflux, 11.5 h 9: TiCl4 / CH2Cl2 / 0.02 h / 0 °C 10: 5.7 mg / pyridinium dichromate / CH2Cl2 / 24 h / Ambient temperature View Scheme

1: pyridinium chlorochromate; NaOAc; molecular sieves / CH2Cl2 / 1 h / Ambient temperature 2: 1.) n-BuLi in n-hexane/diisopropylamine / 1.) THF, -74 deg C, 80 min,2.) -70 deg C, 30 min 3: 84 percent / (i-Pr)2NEt / CH2Cl2 / 89 h / Ambient temperature 4: 82 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 5: 84 percent / quinoline; H2 / 5percent Pd/BaSO4 / methanol / Ambient temperature 6: LiOH*H2O / H2O; tetrahydrofuran / 5 h / Ambient temperature 7: 1.) 2,4,6-trichlorobenzoyl chloride, NEt3,2.) 4-(dimethylamino)pyridine / 1.) THF, room temp., 8.5 h, 2.) toluene, reflux, 11.5 h 8: TiCl4 / CH2Cl2 / 0.02 h / 0 °C 9: 5.7 mg / pyridinium dichromate / CH2Cl2 / 24 h / Ambient temperature View Scheme

1: 1.) Et3N / 1) CH3CN, rt, 30 min; 2) CH3CN, rt, 24 h 2: 45 percent / TiCl3, NH4OAc / tetrahydrofuran; H2O / 2 h / Ambient temperature; pH 5.1 3: 81 percent / LiOH / tetrahydrofuran; H2O / 6 h / 50 °C 4: 1.) Et3N, 2,4,6-trichlorobenzoyl chloride, 2.) DMAP / 1) THF, rt, 6 h; 2) toluene, reflux, 6 h View Scheme

1: 81 percent / LiOH / tetrahydrofuran; H2O / 6 h / 50 °C 2: 1.) Et3N, 2,4,6-trichlorobenzoyl chloride, 2.) DMAP / 1) THF, rt, 6 h; 2) toluene, reflux, 6 h View Scheme

1: 45 percent / TiCl3, NH4OAc / tetrahydrofuran; H2O / 2 h / Ambient temperature; pH 5.1 2: 81 percent / LiOH / tetrahydrofuran; H2O / 6 h / 50 °C 3: 1.) Et3N, 2,4,6-trichlorobenzoyl chloride, 2.) DMAP / 1) THF, rt, 6 h; 2) toluene, reflux, 6 h View Scheme

dipyridinium dichromate in dichloromethane 73 h; Ambient temperature; Yield given;